title: Pd-catalyzed bis-cyclization/dimerization reactions of ω-aminovinyl halides.
abstract: Palladium is shown to catalyze the dimerization and cyclization of vinyl halides to generate pyrrolidine and piperidine dimers connected by a trans-ethylene bridge. The reaction tolerates a variety of N-alkyl substituents, including adamantyl. This remarkable dimerization reaction generates the skeleton of the alkaloid hyalbidone in a single step. A crossover experiment with a vinyl halide and a vinyl bromide is consistent with a Michael-type addition to a vinylpalladium cation to generate a Pd(0) alkylidene intermediate.
authors.affiliation: Departmentof Chemistry, University of California at Irvine, Irvine, California 92697-2025, USA.
authors.forename: Avinash
authors.initials: A
authors.lastname: Khanna
authors.forename: Ilandari Dewage Udara Anulal
authors.initials: ID
authors.lastname: Premachandra
authors.forename: Paul D
authors.initials: PD
authors.lastname: Sung
authors.forename: David L
authors.initials: DL
authors.lastname: Van Vranken